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Impact of chirality on peculiar ibuprofen molecular dynamics: hydrogen bonding organizations and syn vs anti carboxylic group conformation

Abstract

Studies of the impact of chirality on the amorphous states are scarce. Here, we present combined dielectric relaxation spectroscopy (DRS) experiments and molecular dynamics (MD) simulations investigations of the homochiral and racemic ibuprofen in the liquid, undercooled liquid and glassy states. The influence of chirality is particularly investigated on the syn and anti conformations of the —COOH moiety of the ibuprofen molecule and its link to the peculiar Debye-like dynamical process detected in this compound. Most of the studied properties are found to be nearly identical in the homochiral and racemic systems. But the polarity and intensity of the Debye-like process are clearly found to be more intense in the racemic mixture than in the enantiomerically pure ibuprofen. The difference is explained by the higher population of the anti conformation (with the higher dipole moment) and the lower population of hydrogen bonded cyclic dimers that can be transiently formed in the racemic mixture.

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Publication details

The article was received on 31 Jul 2018, accepted on 31 Oct 2018 and first published on 31 Oct 2018


Article type: Paper
DOI: 10.1039/C8CP04837A
Citation: Phys. Chem. Chem. Phys., 2018, Accepted Manuscript
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    Impact of chirality on peculiar ibuprofen molecular dynamics: hydrogen bonding organizations and syn vs anti carboxylic group conformation

    M. T. Ottou Abe, T. M. Viciosa, N. T. Correia and F. Affouard, Phys. Chem. Chem. Phys., 2018, Accepted Manuscript , DOI: 10.1039/C8CP04837A

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